AI Article Synopsis
- A clear distinction is made between two photochemical reactions involving (o/p)-hydroxy-o-methylphenacyl esters: a triplet state Type II H-abstraction reaction and a photo-Favorskii rearrangement.
- The transition from an anhydrous pathway, which produces indanones, to an aqueous-dependent pathway, yielding benzofuranones, happens sharply around low water concentrations (approximately 8%).
- The impressive yields from these reactions indicate potential for synthetic applications.
Article Abstract
A clean bifurcation between two important photochemical reactions through competition of a triplet state Type II H-abstraction reaction with a photo-Favorskii rearrangement for (o/p)-hydroxy-o-methylphenacyl esters that depends on the water content of the solvent has been established. The switch from the anhydrous Type II pathway that yields indanones to the aqueous-dependent pathway producing benzofuranones occurs abruptly at low water concentrations (~8%). The surprisingly clean yields suggest that such reactions are synthetically promising.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3039054 | PMC |
| http://dx.doi.org/10.1021/ol102887f | DOI Listing |
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